Copper-Catalyzed Synthesis of Benzofuropyrimidoisoindole Derivatives

doi:10.6023/cjoc202404005

Chinese Journal of Organic Chemistry Previous Articles Next Articles

ARTICLE

铜催化苯并呋喃并嘧啶并异吲哚衍生物的合成

何姮^a, 吕兰兰^a,*, 刘建全^a, 王香善^a,*

^a江苏师范大学化学与材料科学学院江苏徐州 221116

收稿日期:2024-04-05 修回日期:2024-05-14
基金资助:
江苏省优秀青年基金(No. BK20211607 )和江苏省高等学校重点学科建设计划的资助.

Copper-Catalyzed Synthesis of Benzofuropyrimidoisoindole Derivatives

Heng He^a, Lanlan Lv^a,*, Jian-Quan Liu^a, Xiang-Shan Wang^a,*

^aSchool of Chemistry and Materials Science, Jiangsu Normal University, Xuzhou Jiangsu, 221116

Received:2024-04-05 Revised:2024-05-14
Contact: *E-mail: lvll800@126.com; xswang@jsnu.edu.cn.
Supported by:
Outstanding Youth Fund of Jiangsu Province (BK20211607), the Priority Academic Program Development of Jiangsu Higher Education Institutions.

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Abstract

A copper-catalyzed Sonogashira coupling reaction and 5-exo-dig aminocyclization between 2-(2-bromophenyl)benzofuro[3,2-d]pyrimidin-4(3H)-ones and terminal alkynes were disclosed. The protocol allowed access to a series of 8-benzylidene benzofuro[3',2':4,5]pyrimido[2,1-a]isoindol-6(8H)-one derivatives with high efficiency, broad substrate scope, and excellent functional group compatibility, which were shown to be of a single (E)-configuration by X-ray diffraction analysis.

Key words: Benzofuropyrimidoisoindole, Sonogashira coupling, Acetylene hydroamination, CuI

Cite this article

Heng He, Lanlan Lv, Jian-Quan Liu, Xiang-Shan Wang. Copper-Catalyzed Synthesis of Benzofuropyrimidoisoindole Derivatives[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202404005.

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[1] Jiang X.; Tang T.; Wang J.-M.; Chen Z.; Zhu Y.-M.; Ji S.-J.,J. Org. Chem. 2014, 79, 5082-5087.
[2] Verma V.; Schafer L. L.,J. Org. Chem. 2023, 88, 1378-1384.
[3] Hosseinzadeh Z.; Ramazani A.; Razzaghi-Asl, N., Curr. Org. Chem. 2018, 22, 2256-2279.
[4] Mermer A.; Keles T.; Sirin, Y. Bioorg. Chem. 2021, 114, 105076.
[5] Parshikov I. A.; Silva E. O.; Furtado N. A.J. C., Appl. Microbiol. Biot. 2014, 98, 1497-1506.
[6] Kharazi M.; Saien J.; Asadabadi S.,Topics Curr. Chem. 2021, 380, 5.
[7] Chainikova E.; Safiullin R.; Spirikhin L.; Erastov A.,Tetrahedron Lett. 2013, 54, 2140-2142.
[8] Gordon E. M.; Barrett R. W.; Dower W. J.; Fodor S. P.A.; Gallop, M. A., J. Med. Chem. 1994, 37, 1385-1401.
[9] Lai X.; Liu J.-B.; Wang Y.-C.; Qiu, G. Chem. Commun. 2021, 57, 2077-2080.
[10] Ding Q.; Ye Y.; Fan R.; Wu J.,J. Org. Chem. 2007, 72, 5439-5442.
[11] He Y.; Cheng C.; Chen B.; Duan K.; Zhuang Y.; Yuan B.; Zhang M.; Zhou Y.; Zhou Z.; Su Y.-J.; Cao R.; Qiu, L. Org. Lett. 2014, 16, 6366-6369.
[12] Li B.; Zhang J.; Li L.; Chen, G. Chem. Sci. 2021, 12, 2504-2508.
[13] Malet-Martino, M.; Jolimaitre, P.; Martino, R., Anti-Cancer Agent. Me. 2002, 2, 267-310.
[14] van Kuilenburg, A. B. P., Eur. J. Cancer 2004, 40, 939-950.
[15] Gölcü A.; Muslu H.; Kılıçaslan D.; Çeşme M.; Eren Ö.; Ataş F.; Demirtaş İ.,J. Mol. Struct. 2016, 1119, 96-109.
[16] Rashid, H. u.; Martines, M. A. U.; Duarte, A. P.; Jorge, J.; Rasool, S.; Muhammad, R.; Ahmad, N.; Umar, M. N., RSC Adv. 2021, 11, 6060-6098.
[17] Zhuang J.; Ma S., ChemMedChem 2020, 15, 1875-1886.
[18] Khanam H.; Shamsuzzaman Eur. J. Med. Chem. 2015, 97, 483-504.
[19] Xu Z.; Xu D.; Zhou W.; Zhang, X., Curr. Top. Med.Chem. 2022, 22, 64-82.
[20] Abbas A. A.; Dawood K. M.,Expert Opin. Drug Dis. 2022, 17, 1357-1376.
[21] Cottineau B.; Toto P.; Marot C.; Pipaud A.; Chenault, J., Bioorg. Med. Chem.Lett. 2002, 12, 2105-2108.
[22] Xie Y.-S.; Kumar D.; Bodduri V. D.V.; Tarani, P. S.; Zhao, B.-X.; Miao, J.-Y.; Jang, K.; Shin, D.-S., Tetrahedron Lett. 2014, 55, 2796-2800.
[23] Koca M.; Servi S.; Kirilmis C.; Ahmedzade M.; Kazaz C.; Özbek B.; Ötük, G., Eur. J. Med.Chem. 2005, 40, 1351-1358.
[24] Xie F.; Zhu H.; Zhang H.; Lang Q.; Tang L.; Huang Q.; Yu, L. Eur. J.Med.Chem. 2015, 89, 310-319.
[25] Spaniol M.; Bracher R.; Ha H. R.; Follath F.; Krähenbühl S.,J. Hepatol. 2001, 35, 628-636.
[26] Tyltin A. K.; Kovtunenko V. A.; Rytova N. N.; Babichev, F. S., Chem. Heterocycl.Com+ 1977, 13, 912-914.
[27] Kysil A. I.; Voitenko Z. V.; Wolf, J.-G., Collect. Czech. Chem.C. 2008, 73, 247-257.
[28] Voitenko Z. V.; Kysil A. I.; Wolf, J. G., CR. Chim. 2007, 10, 813-819.
[29] He H.; Liu J.-Q.; Wang, X.-S., Org. Biomol. Chem. 2023, 21, 7886-7890.
[30] Geng X.; Shatskiy A.; Alvey G. R.; Liu J.-Q.; Kärkäs M. D.; Wang, X.-S. Org. Lett. 2022, 24, 9194-9199.
[31] Chen Y.; Shatskiy A.; Liu J.-Q.; Kärkäs M. D.; Wang, X.-S. Org. Lett. 2021, 23, 7555-7560.
[32] Wang Y.-C.; Chen X.; Alvey G. R.; Shatskiy A.; Liu J.-Q.; Kärkäs M. D.; Wang, X.-S., Org. Chem. Front. 2022, 9, 4158-4163.
[33] Xu L.; Liu X.; Alvey G. R.; Shatskiy A.; Liu J.-Q.; Kärkäs M. D.; Wang, X.-S. Org. Lett. 2022, 24, 4513-4518.
[34] Jiang W.; Li Y.; Liu J.-Q.; Wang, X.-S. Org. Lett. 2023, 25, 5123-5127.
[35] Geng X.; He H.; Shatskiy A.; Stepanova E. V.; Alvey G. R.; Liu J.-Q.; Kärkäs M. D.; Wang X.-S.,J. Org. Chem. 2023, 88, 12738-12743.
[36] Ashfaq U. A.; Javed T.; Rehman S.; Nawaz Z.; Riazuddin, S. Virol. J. 2011, 8, 163.
[37] Cao X.; Zhang Z.; Li J.; Shi B.; Li M.; Zhang G.; Zhang X.,J. Org. Chem. 2022, 87, 13672-13682.
[38] Yang Xiong, G. Z., Chin. J. Org. Chem. 2023, 43, 1890-1892.
[39] Song D.; Moon H.; Jung K.; Yeom M.; Kim H.; Han S.; An D.; Oh J.; Kim J.; Park B.; Kang, B. Virol. J. 2011, 8, 1.

铜催化苯并呋喃并嘧啶并异吲哚衍生物的合成

Copper-Catalyzed Synthesis of Benzofuropyrimidoisoindole Derivatives

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